75867-40-2

Usage

Uses

Used in Organic Synthesis:
4-Trimethylsilyl ethynyl benzonitrile (97) is used as a building block for the synthesis of functionalized aromatic compounds. Its high reactivity and versatility in forming carbon-carbon and carbon-heteroatom bonds make it a valuable reagent in this application.
Used in Pharmaceutical Production:
4-Trimethylsilyl ethynyl benzonitrile (97) is used as a reagent in the production of pharmaceuticals. Its stability and protective trimethylsilyl group during chemical reactions contribute to the synthesis of various medicinal compounds.
Used in Agrochemical Production:
4-Trimethylsilyl ethynyl benzonitrile (97) is utilized as a reagent in the production of agrochemicals. Its role in the synthesis of functionalized aromatic compounds aids in the development of effective agricultural chemicals.
Used in Materials Science:
4-Trimethylsilyl ethynyl benzonitrile (97) is employed in materials science for the synthesis of advanced materials. Its unique properties and reactivity contribute to the development of new materials with specific functions and properties.
Used in Molecular Interaction and Surface Chemistry Studies:
4-Trimethylsilyl ethynyl benzonitrile (97) is used as a probe molecule in studies of molecular interactions and surface chemistry. Its unique structure and properties make it a valuable tool for understanding complex chemical processes and interactions at the molecular level.

InChI:InChI=1/C12H13NSi/c1-14(2,3)9-8-11-4-6-12(10-13)7-5-11/h4-7H,1-3H3

Upstream product

• 623-00-7 4-bromobenzenecarbonitrile 
• 1066-54-2 trimethylsilylacetylene 
• 3032-92-6 4-cyanophenylacetylene 
• 996-50-9 N,N-diethyl-1,1,1-trimethylsilanamine 
• 3058-39-7 4-iodobenzonitrile 
• 767-00-0 4-cyanophenol 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 78389-87-4 ((trimethylsilyl)ethynyl)zinc(II) chloride 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 106-37-6 1.4-dibromobenzene 
• 16116-78-2 (4-bromophenyl)(trimethylsilyl)acetylene 
• 75-77-4 chloro-trimethyl-silane 
• 66107-32-2 4-cyanophenyl trifluoromethanesulfonate 

Downstream Products

• 69975-66-2 1-oxo-6-indanecarbonitrile 
• 3032-92-6 4-cyanophenylacetylene 
• 187876-99-9 4-Trimethylsilanylethynyl-thiobenzamide 
• 56982-37-7 4-[(4-methoxyphenyl)ethynyl]benzonitrile 
• 29822-79-5 4-(2-phenylethynyl)benzonitrile 
• 848568-92-3 tris-4,4',4''-(4-cyanophenylethynyl)triphenylamine 
• 214401-46-4 ethyl {7-[2-(4-cyanophenyl)ethyl]-1,2,3,4-tetrahydro-2-naphthalenyl}acetate 
• 863640-43-1 4-(trimethylsilanylethynyl)benzamide 
• 919791-41-6 4-(chloroethynyl)benzonitrile 
• 1253299-41-0 12c-(4-cyanophenyl)ethynyl-4,8,12-tri-n-octyl-4,8,12-triazatriangulene 

Relevant academic research and scientific papers

Effect of the π-bridge on the light absorption and emission in push-pull coumarins and on their supramolecular organization

A family of eight π-extended push–pull coumarins with cross-conjugated (amide) and directly conjugated (p-phenylene, alkyne, alkene) bridges were synthesized through a convergent strategy. Using an experimentally calibrated computational protocol, their UV–Visible light absorption and emission spectra in solution were investigated. Remarkably, amide-, alkyne- and alkene-bridges undergo comparable vertical excitations. The different nature of these bridges manifests during excited-state relaxation and fluorescence. We predict that these molecules can serve as building blocks for p-type semiconductors with low reorganization energies, below 0.2 eV. Since solid-state self-assembly is crucial for this application, we examined the effect of the π-bridge over the supramolecular organization in this family of compounds to determine if stacking prevails in these π-extended coumarin derivatives. Amide and alkyne spacers allow coplanar conformations which crystallize readily; p-phenylene hinders planarity yet allows facile crystallization; alkene-bridged molecules eluded all crystallization attempts. All the crystals obtained feature dense face-to-face π-stacking with 3.5–3.7 ? interlayer distances, expected to facilitate charge transfer processes in the solid state.

Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes

A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.

Ynonylation of Acyl Radicals by Electroinduced Homolysis of 4-Acyl-1,4-dihydropyridines

Herein we report the conversion of 4-Acyl-1,4-dihydropyridines (DHPs) into ynones under electrochemical conditions. The reaction proceeds via the homolysis of acyl-DHP under electron activation. The resulting acyl radicals react with hypervalent iodine(III) reagents to form the target ynones or ynamides in acceptable yields. This mild reaction condition allows wider functionality tolerance that includes halides, carboxylates, or alkenes. The synthetic utility of this methodology is further demonstrated by the late-stage modification of complex molecules.

Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.

Click Variations on the Synthesis of 2-Nitrophenyl-4-aryl-1,2,3-triazoles without Isolation of 2-Nitrophenyl Azides

We report a series of efficient procedures to prepare 2-nitrophenyl-4-aryl-1,2,3-triazoles avoiding the isolation of potentially hazardous 2-nitrophenyl azides. An organocatalyzed azide-enolate variant allows efficient access to the target compounds while

γ-Carboline synthesis enabled by Rh(iii)-catalysed regioselective C-H annulation

A redox-neutral Rh(iii)-catalyzed C-H annulation of indolyl oximes was developed. Relying on the use of various alkynyl silanes as the terminal alkyne surrogates, the reaction exhibited a reverse regioselectivity, thus giving an exclusive and easy way for the synthesis of a wide range of substituent free γ-carbolines at C3 position with high efficiency. Deuterium-labelling experiments and kinetic analysis have preliminarily shed light on the working mode of this catalytic system. This journal is

Ratiometric sensing of fluoride ions using Raman spectroscopy

Ratiometric Raman spectroscopy represents a novel sensing approach for the detection of fluoride anions based on alkyne desilylation chemistry. This method enables rapid, anion selective and highly sensitive detection of fluoride in a simple paper-based a

Nickel-Catalyzed Sonogashira C(sp)-C(sp2) Coupling through Visible-Light Sensitization

An efficient method for visible-light-initiated, nickel-catalyzed Sonogashira C(sp)-C(sp2) coupling has been developed via an energy-transfer mode. Thioxanthen-9-one as a photosensitizer could significantly accelerate the arylation of alkynes with a wide

A convenient reagent for the conversion of aldoximes into nitriles and isonitriles

For the dehydroxylation of aldoximes with 4-nitro-1-((trifluoromethyl)sulfonyl)-imidazole (NTSI), slight modifications of reaction conditions resulted in significantly different reaction paths to provide either nitriles or isonitriles. The challenging conversion of aldoximes into isonitriles was achieved under mild conditions.

C-Terminal Bioconjugation of Peptides through Photoredox Catalyzed Decarboxylative Alkynylation

We report the first decarboxylative alkynylation of the C-terminus of peptides starting from free carboxylic acids. The reaction is fast, metal-free, and proceeds cleanly to afford alkynylated peptides with a broad tolerance for the C-terminal amino acid. By the use of hypervalent iodine reagents, the introduction of a broad range of functional groups was successful. C-terminal selectivity was achieved by differentiation of the oxidation potentials of the carboxylic acids based on the use of fine-tuned organic dyes.